Plenty of technology companies struggle to put new inventions in the right context. Many call on artists to help demonstrate what’s possible. Google is systematically handing artists its HTC Vive VR headsets, which have software that enables 3D sketching, in hopes that they can demonstrate creative uses for the technology. Microsoft just presented an interactive installation, with Grimes’ music, that shows off its Kinect motion-sensing technology. There’s no shortage of similar examples, and just as much excitement to do more of it.

Artist / technologist collaborations aren’t exactly a new idea, but Seven On Seven is one of the most notable events promoting them. It’s an annual art tech hackathon hosted by Rhizome, an organization that commissions, exhibits, preserves and creates art engaged with digital culture, and the New Museum in New York City. Seven on Seven pairs seven artists with seven technologists and asks each pair to make something — anything — and then talk about it in front of a live audience.

In his opening remarks before the demonstrations this weekend, Rhizome artistic director Michael Connor said of the arrangement,”It’s pretty bonkers. There’s nothing else quite like this.” He applauded the bravery of the participants, who go into this as an experiment that’s not at all sure to succeed: “It’s risky, things can go really right or really wrong. Everything is so polished in the world, that risk is a big part of Seven on Seven.”

Here’s what they made this year:

Some pairs were able to make working prototypes. Claire Evans, the YACHT singer and songwriter, and partner Tracy Chou, a software developer at Pinterest, coded a play, performed on a screen and starring bots, whose characters are randomly assigned gender with each performance.

Evans explained they wanted the gender shuffle to be a “creative test for your own gender biases” and help viewers tease out their assumptions and expectations about men, women and AI characters. Chou added that they thought this was important because AI has been “traditionally” gendered so far: Siri and Alexa do chores, Watson cures cancer and wins jeopardy. With this short play, that social assumption in technology is challenged.

Another prototype that seems applicable in educational or empathy-building contexts: the emotion-reading app built by artist Jennifer Steinkamp and engineer Rana El-Kaliouby, cofounder of an emotion measurement technology company called Affectiva. When a user opens the app, their face appears beneath a gesture-tracking mask, which records how their facial gestures indicate being sad, mad, calm or ecstatic.

Some prototypes didn’t have an artistic or practical mission. Filmmaker and novelist Miranda July worked with Paul Ford (better known by his twitter handle @ftrain and for his Bloomberg opus, What is Code?) to tell a story using found materials from attendees’ social media profiles. Ford made a widget to help search the attendees’ digital footprints. July asked a private investigator to help. Together, they performed an uncomfortably intimate and unsurprisingly banal run-through of details shared online, complete with pictures of the room’s mothers, dinners and favorite sunsets. They said they made it without an agenda, and were working up until presentation time to make it less boring.

The Seven on Seven organizers are quick to point out that not every experiment is meant to productive. The pure act of experimenting is highly valued.

To that end, some projects focused on the hypothetical instead of practical. Jenna Wortham, a staff writer for The New York Times Magazine, and rapper JUNGLEPUSSY presented their idea for a pharmaceutical to facilitate offline person-to-person connections in the real world. Google Open Source Research and Security Group founder Meredith Whittaker and artist Ingrid Burrington poked fun at tech and academia with a farcical comedy about their groundbreaking “discovery” of a magical, otherworldly power structure suspiciously similar to the mysticism and intentionally confusing inner workings of Silicon Valley.

Though the conference has been held annually since 2010, this was the first time partners were given more than 24 hours to work on their projects together. Connor mentioned there had “always been a sense of reality TV panic,” when he observed previous participants frantically hacking together ideas the day of their presentation. This time, they had several weeks.

With the extra time, the collaborations were much more likely to happen remotely. Several met each other the day of the presentations, even though they had spent weeks communicating about personalities, work styles and areas of interest. Evans remembers first talking to her partner Chou while driving through Texas on tour with her band, and coming up with the idea for their play sitting at a merch table in Santa Cruz. Chou mentioned she’s used to work like this, and often does her other projects with remote collaborators, using tools like Slack and Google drive.

The extra time also gave collaborators more opportunities to fail and iterate. Wortham and JUNGLEPUSSY’s concept drug was something they hit on after deciding a “tinder for showing people pages of your journal” wasn’t high-tech enough.

The extra time also lets partners appreciate each other’s respective skills on a deeper level. Evans and Chou were able to adjust the code to fit their story better. Evans, wanting the robots to speak with more dramatic pauses, learned to put periods mid-sentence, essentially “programming” her language to fit better with Chou’s. And in turn, Chou thought to develop a ”(beat)” a command in her code, so the pauses wouldn’t have to disrupt the script as much.

Evans says of her technologist partner, “She can do things that are basically magic to me.” Chou was quick to say she felt the same way about her artist counterpart.